RU2015155032A - TYLOSINE DERIVATIVES AND METHOD FOR PRODUCING THEM - Google Patents

TYLOSINE DERIVATIVES AND METHOD FOR PRODUCING THEM Download PDF

Info

Publication number
RU2015155032A
RU2015155032A RU2015155032A RU2015155032A RU2015155032A RU 2015155032 A RU2015155032 A RU 2015155032A RU 2015155032 A RU2015155032 A RU 2015155032A RU 2015155032 A RU2015155032 A RU 2015155032A RU 2015155032 A RU2015155032 A RU 2015155032A
Authority
RU
Russia
Prior art keywords
substituted
heterocycle
aryl
bacterial infections
group
Prior art date
Application number
RU2015155032A
Other languages
Russian (ru)
Other versions
RU2015155032A3 (en
RU2714482C2 (en
Inventor
Герд КЛЕЕФЕЛЬД
Робрехт Фройман
Каролин ЛЮДВИГ
Сатоси Омура
Тосиаки Суназука
Хиросе ТОМОЯСУ
Сугавара АКИХИРО
Сиоми КАЗУРО
Original Assignee
Байер Энимэл Хельс ГмбХ
Китасато Инститьют
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=48463869&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RU2015155032(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Байер Энимэл Хельс ГмбХ, Китасато Инститьют filed Critical Байер Энимэл Хельс ГмбХ
Publication of RU2015155032A publication Critical patent/RU2015155032A/en
Publication of RU2015155032A3 publication Critical patent/RU2015155032A3/ru
Application granted granted Critical
Publication of RU2714482C2 publication Critical patent/RU2714482C2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Claims (39)

1. Соединение, представленное формулой (IIa):1. The compound represented by formula (IIa):
Figure 00000001
Figure 00000001
 или его фармацевтически приемлемая соль, сложный эфир, пролекарство или сольват;or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof; где R11 и R12 каждый независимо выбирается изwhere R 11 and R 12 each independently selected from водорода;hydrogen; -СНО;-CHO; C1-С6-Х, где X выбирается из группы, состоящей из гидроксила или защищенного гидроксила, галогена и N3;C 1 -C 6 -X, where X is selected from the group consisting of hydroxyl or protected hydroxyl, halogen and N 3 ; CN;CN; С1-С6-алкила, необязательно замещенного одним или более заместителями, выбранными из группы, состоящей из галогена, арила, замещенного арила, гетероцикла и замещенного гетероцикла;C1-C6 alkyl optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocycle, and substituted heterocycle; С2-С6-алкенила, необязательно замещенного одним или более заместителями, выбранными из группы, состоящей из галогена, арила, замещенного арила,C2-C6 alkenyl optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, гетероцикла и замещенного гетероцикла;heterocycle and substituted heterocycle; С2-С6-алкинила, необязательно замещенного одним или более заместителями, выбранными из группы, состоящей из галогена, арила, замещенного арила, гетероцикла и замещенного гетероцикла;C2-C6 alkynyl optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocycle, and substituted heterocycle; С3-С14-циклоалкила;C3-C14 cycloalkyl; замещенного С3-С14-циклоалкила;substituted C3-C14 cycloalkyl; арила;aryl; замещенного арила;substituted aryl; гетероцикла;heterocycle; замещенного гетероцикла;substituted heterocycle; или R11 и R12, взятые вместе с атомом азота, с которым они связаны, образуют N3 или 3-7-членное кольцо, которое может необязательно содержать гетерогруппу, выбранную из группы, состоящей из -О-, -NH-, -N(С1-С6-алкила)-, -N(арила)-, -N(гетероарила)-, -S-, -S(O)- и -S(О)2-; C3-C14 циклоалкила; иor R 11 and R 12 taken together with the nitrogen atom to which they are bonded form an N 3 or 3-7 membered ring, which may optionally contain a hetero group selected from the group consisting of —O—, —NH—, N (C1-C6-alkyl) -, -N (aryl) -, -N (heteroaryl) -, -S-, -S (O) - and -S (O) 2 -; C3-C14 cycloalkyl; and где R5 представляет собойwhere R 5 represents водород;hydrogen; гидроксил;hydroxyl; защищенный гидроксил;protected hydroxyl; галоген;halogen; -Ν3; или-Ν 3 ; or N-Y2, где каждый Y независимо выбирается из группы, состоящей из водорода и С1-С6-алкила, или два Y, взятые вместе с атомом азота, с которым они связаны, образуют 3- 7-членное кольцо.NY 2 , where each Y is independently selected from the group consisting of hydrogen and C1-C6 alkyl, or two Y taken together with the nitrogen atom to which they are bonded form a 3 to 7 membered ring. 2. Соединение по п. 1, где:2. The compound according to claim 1, where: R5 представляет собой гидрокси.R 5 represents hydroxy. 3. Соединение по п. 1 или 2, где:3. The compound according to claim 1 or 2, where: по меньшей мере R11 или R12 представляет собой С1-С6-алкил, необязательно замещенный одним или более заместителями, выбранными из группы, состоящей из галогена, арила, замещенного арила, гетероцикла и замещенного гетероцикла.at least R 11 or R 12 is C1-C6 alkyl optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocycle, and substituted heterocycle. 4. Соединение по п. 3, где:4. The compound according to claim 3, where: по меньшей мере R11 или R12 представляет собой С1-С6-алкил, замещенный одним заместителем, выбранным из группы, состоящей из гетероцикла и замещенного гетероцикла.at least R 11 or R 12 is C1-C6 alkyl substituted with one substituent selected from the group consisting of a heterocycle and a substituted heterocycle. 5. Соединение по любому одному из пп. 1-4 для применения в качестве лекарственного средства.5. The compound according to any one of paragraphs. 1-4 for use as a medicine. 6. Соединение по любому одному из пп. 1-4 для применения для лечения или профилактики бактериальных инфекций или нарушений, связанных с бактериальными инфекциями, у животного.6. The compound according to any one of paragraphs. 1-4 for use in the treatment or prevention of bacterial infections or disorders associated with bacterial infections in an animal. 7. Применение соединения по любому одному из пп. 1-4 для получения фармацевтической или ветеринарной композиции для лечения или профилактики бактериальных инфекций или нарушений, связанных с бактериальными инфекциями, у животного.7. The use of compounds according to any one of paragraphs. 1-4 to obtain a pharmaceutical or veterinary composition for the treatment or prevention of bacterial infections or disorders associated with bacterial infections in an animal. 8. Способ лечения или профилактики бактериальных инфекций или нарушений, связанных с бактериальными инфекциями, у животного, где способ включает введение животному терапевтически эффективного количества соединения по п. 1.8. A method for treating or preventing bacterial infections or disorders associated with bacterial infections in an animal, wherein the method comprises administering to the animal a therapeutically effective amount of a compound according to claim 1. 9. Фармацевтическая или ветеринарная композиция, содержащая соединение по любому одному из пп. 1-4 и по меньшей мере один фармацевтически приемлемый носитель.9. A pharmaceutical or veterinary composition comprising a compound according to any one of claims. 1-4 and at least one pharmaceutically acceptable carrier. 10. Фармацевтическая или ветеринарная композиция по п. 9 для применения для лечения или профилактики бактериальных инфекций или нарушений, связанных с бактериальными инфекциями, у животного.10. The pharmaceutical or veterinary composition of claim 9 for use in the treatment or prevention of bacterial infections or disorders associated with bacterial infections. 11. Способ лечения или профилактики бактериальных инфекций или нарушений, связанных с бактериальными инфекциями, у животного, где способ включает введение животному терапевтически эффективного количества композиции по п. 9.11. A method of treating or preventing bacterial infections or disorders associated with bacterial infections in an animal, wherein the method comprises administering to the animal a therapeutically effective amount of a composition according to claim 9.
RU2015155032A 2013-05-23 2014-05-23 Tylosin derivatives and method for production thereof RU2714482C2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13169009 2013-05-23
EP13169009.1 2013-05-23
PCT/EP2014/060665 WO2014187957A1 (en) 2013-05-23 2014-05-23 Tylosin derivatives and method for preparation thereof

Publications (3)

Publication Number Publication Date
RU2015155032A true RU2015155032A (en) 2017-06-27
RU2015155032A3 RU2015155032A3 (en) 2018-04-28
RU2714482C2 RU2714482C2 (en) 2020-02-18

Family

ID=48463869

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2015155032A RU2714482C2 (en) 2013-05-23 2014-05-23 Tylosin derivatives and method for production thereof

Country Status (26)

Country Link
US (1) US9771389B2 (en)
EP (1) EP2999707B1 (en)
JP (1) JP6494600B2 (en)
KR (1) KR102307218B1 (en)
CN (1) CN105408340B (en)
AU (1) AU2014270353B2 (en)
BR (1) BR112015029260A2 (en)
CA (1) CA2913098C (en)
CL (1) CL2015003433A1 (en)
DK (1) DK2999707T3 (en)
ES (1) ES2669615T3 (en)
HK (1) HK1216753A1 (en)
HR (1) HRP20180877T1 (en)
HU (1) HUE037868T2 (en)
IL (1) IL242543B (en)
MX (1) MX361808B (en)
MY (1) MY184630A (en)
NO (1) NO2999707T3 (en)
PE (1) PE20160207A1 (en)
PL (1) PL2999707T3 (en)
PT (1) PT2999707T (en)
RU (1) RU2714482C2 (en)
SI (1) SI2999707T1 (en)
TR (1) TR201809189T4 (en)
UA (1) UA117751C2 (en)
WO (1) WO2014187957A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160303242A1 (en) 2013-12-09 2016-10-20 Durect Corporation Pharmaceutically Active Agent Complexes, Polymer Complexes, and Compositions and Methods Involving the Same
CN110590885A (en) * 2019-09-30 2019-12-20 郑州大学 20-substituted-5-O-mycaminosyl-tylonolide derivatives
CN112898361A (en) * 2021-02-01 2021-06-04 郑州大学 5-O-mycylamine glycosyl tylosin lactone derivative and preparation method and application thereof
WO2023230702A1 (en) * 2022-06-03 2023-12-07 University Of Manitoba Novel antimicrobial compounds isolated using a machine learning model trained on a high-throughput antibacterial screen

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL69666A (en) * 1982-09-13 1987-10-20 Lilly Co Eli 20-amino-20-deoxo-5-o-mycaminosyl-23-o-mycinosyltylonolide derivatives,their preparation and veterinary antibiotic use
US4443436A (en) * 1982-09-13 1984-04-17 Eli Lilly And Company C-20-Modified macrolide derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, and lactenocin
ZA841277B (en) * 1983-02-28 1985-09-25 Lilly Co Eli C-20-and c-23-modified macrolide derivatives
US4468511A (en) * 1983-02-28 1984-08-28 Eli Lilly And Company C-20- And C-23-Modified macrolide derivatives
IL71032A0 (en) 1983-02-28 1984-05-31 Lilly Co Eli C-20 and c-23-modified macrolide derivatives
JPS59186996A (en) * 1983-04-05 1984-10-23 Microbial Chem Res Found 20-deoxy-20-substituted amino-mycaminosylrelonolide
US4921947A (en) * 1986-03-31 1990-05-01 Eli Lilly And Company Process for preparing macrolide derivatives
EP0262903A3 (en) * 1986-09-29 1988-11-02 Eli Lilly And Company New acyl derivatives of 20-modified tylosin and desmycosin compounds
TW226373B (en) * 1992-07-15 1994-07-11 Pfizer
ZA939428B (en) 1992-12-21 1995-06-15 Lilly Co Eli Therapeutic for gram-positive diseases of aquatic species
WO1996009312A1 (en) 1994-09-22 1996-03-28 Pfizer Inc. Antibiotic macrolides
ATE261450T1 (en) * 1999-08-30 2004-03-15 Zaidan Hojin Biseibutsu MACROLIDE ANTIBIOTICS AND TREATMENT OF PASTEURELLOSIS
US6506885B1 (en) * 2001-09-27 2003-01-14 The United States Of America As Represented By The Secretary Of Agriculture Monoclonal antibodies to the drug tilmicosin and a method for detecting the same
US6576615B2 (en) 2001-11-08 2003-06-10 Enanta Pharmaceuticals, Inc. 4′-O-substituted tylosin analogs
US6664240B2 (en) * 2001-11-15 2003-12-16 Enanta Pharmaceuticals, Inc. Tylosin derivatives having antibacterial activity
US6710034B2 (en) 2002-04-19 2004-03-23 Enanta Pharmaceuticals, Inc. 5-O-mycaminosyltylonide derivatives
US6753415B2 (en) 2002-04-19 2004-06-22 Enanta Pharmaceuticals, Inc. 23-O-substituted 5-O-mycaminosyltylonide derivatives
WO2005118610A2 (en) 2004-06-01 2005-12-15 Rib-X Pharmaceuticals, Inc. Macrocyclic compounds and methods of making and using the same
US7247617B2 (en) * 2004-07-13 2007-07-24 Kosan Biosciences Incorporated Sixteen-member macrolide antiinfective agents
US7282487B2 (en) * 2004-10-28 2007-10-16 Idexx Laboratories Method for treating bacterial infections in horses or pigs with tilmicosin
DE102005061326A1 (en) 2005-12-20 2007-06-21 Basell Polyolefine Gmbh Preparation of metallocene compound, useful e.g. in the preparation of isotactic polypropylene, comprises using a cyclopentadienyl derivative that is recycled from the filtrate obtained from the preparation of e.g. metallocene compound
EP2019112A1 (en) * 2007-07-26 2009-01-28 Intervet International BV Macrolide solid-state forms
WO2008012343A2 (en) * 2006-07-28 2008-01-31 Intervet International B.V. Macrolide synthesis process
UA98303C2 (en) * 2006-07-28 2012-05-10 Интервет Интернешонал Б.В. Macrolide synthesis process
US20090131343A1 (en) 2007-11-15 2009-05-21 Ly Tam Phan Use of bridged macrolides or tylosin derivatives in treating inflammatory bowel diseases
US20110071096A1 (en) * 2009-09-23 2011-03-24 Idexx Laboratories, Inc. Macrolides Having Antibiotic Activity
SI2782922T1 (en) * 2011-11-25 2018-05-31 Bayer Intellectual Property Gmbh Antibacterial tylosin derivatives and methods for their preparation

Also Published As

Publication number Publication date
CN105408340B (en) 2020-06-12
CA2913098C (en) 2021-11-02
MX2015016118A (en) 2016-06-21
HRP20180877T1 (en) 2018-07-13
US20160108077A1 (en) 2016-04-21
CL2015003433A1 (en) 2016-07-15
EP2999707A1 (en) 2016-03-30
US9771389B2 (en) 2017-09-26
CA2913098A1 (en) 2014-11-27
WO2014187957A1 (en) 2014-11-27
JP2016519153A (en) 2016-06-30
KR20160014656A (en) 2016-02-11
MX361808B (en) 2018-12-14
IL242543B (en) 2020-10-29
SI2999707T1 (en) 2018-07-31
PT2999707T (en) 2018-05-23
TR201809189T4 (en) 2018-07-23
EP2999707B1 (en) 2018-03-28
RU2015155032A3 (en) 2018-04-28
PL2999707T3 (en) 2018-09-28
CN105408340A (en) 2016-03-16
PE20160207A1 (en) 2016-05-22
KR102307218B1 (en) 2021-10-05
JP6494600B2 (en) 2019-04-03
AU2014270353B2 (en) 2018-09-20
BR112015029260A2 (en) 2017-07-25
ES2669615T3 (en) 2018-05-28
NZ714071A (en) 2020-12-18
UA117751C2 (en) 2018-09-25
DK2999707T3 (en) 2018-06-06
NO2999707T3 (en) 2018-08-25
MY184630A (en) 2021-04-11
AU2014270353A1 (en) 2015-11-26
RU2714482C2 (en) 2020-02-18
HK1216753A1 (en) 2016-12-02
HUE037868T2 (en) 2018-09-28

Similar Documents

Publication Publication Date Title
CY1118572T1 (en) CYCLOGAL PRODUCTION
EA201991693A1 (en) PYRIDINE DERIVATIVE AS ASK1 INHIBITOR AND METHOD FOR PRODUCING AND USE
CY1120248T1 (en) IMIDAZO COMPOUNDS [4,5-C] KINOLIN-2-ONE AND THEIR USE IN CANCER TREATMENT
JP2016515561A5 (en)
JP2014511892A5 (en)
RU2017105781A (en) INDOSOLIC COMPOUNDS AS FGFR KINASE INHIBITORS, THEIR PRODUCTION AND APPLICATION
TN2016000090A1 (en) Substituted quinolizine derivatives useful as hiv integrase inhibitors.
JP2016503052A5 (en)
TR201802944T4 (en) DERIVATIVES OF AZAINDAZOL OR DIAZAINDAZOL
AR085004A1 (en) SELECTIVE INHIBITORS OF GLYCOSIDASES AND USES OF THE SAME
IN2014DN07283A (en)
TN2019000170A1 (en) Tetracyclic heterocycle compounds useful as hiv integrase inhibitors
RU2016134751A (en) COMPOUNDS
RU2019142472A (en) Glucuronide prodrugs of Janus kinase inhibitors
PH12021550825A1 (en) Quinoline derivatives as alpha4beta7 integrin inhibitors
JP2014501766A5 (en)
MX2021006544A (en) Cdk9 inhibitors and polymorphs thereof for use as agents for treatment of cancer.
JP2016513696A5 (en)
JP2012513416A5 (en)
CY1121060T1 (en) DERIVATIVES [1,2,4] TRIAZOLO [1,5-A] PYRIMIDINE AS PROTOSAL PROTEASE INHIBITORS FOR THE TREATMENT OF PARASTIC DISEASES SUCH AS LEICHMANASIS
WO2014172188A3 (en) 4-pyridone derivative compounds and uses thereof as hiv integrase inhibitors
RU2015155032A (en) TYLOSINE DERIVATIVES AND METHOD FOR PRODUCING THEM
RU2019142111A (en) ANTI-TUMOR EFFECT AMPLIFIER WITH THE APPLICATION OF A NEW BIPHENYL COMPOUND
RU2013136861A (en) A NEW INDO OR INDAZOLE DERIVATIVE OR ITS SALT
RU2015135824A (en) Bicyclic Compounds of Pyrimidone as LP-PLA2 Inhibitors